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$575,000 Sale Pending
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Property Description
Under contract-accepting backup offers. Whether you're searching for your forever home, a sun-soaked Florida retreat, or a savvy investment property - 1389 Chesterfield Drive has you covered. This stunning coastal gem checks every box, and then some. MOVE-IN READY | NEWLY RENOVATED | NO FLOOD ZONE | NO HOA The hard work is already done: Roof (2023), water heater (2023), 125-amp electrical panel (2022), HVAC (2019), screened lanai (2023), gutters (2023), irrigation pump (2023), and appliances (2023). Pack your bags and start living - this home is ready when you are. A recently completed four-point inspection is available upon request, giving you even greater peace of mind. Tucked into a wonderful, established neighborhood within the city limits of Largo, this beautifully designed 3-bedroom, 2-bath coastal home sits just 10 minutes from the beach. From the moment you step through the front door, something shifts - the coastal vibe wraps around you, and it immediately feels like home with a bright open layout. Luxury vinyl plank flooring flows seamlessly throughout, anchoring the open-concept design. The updated kitchen features spectacular quartz countertops, handcrafted tile backsplash, new stainless steel appliances, a designer range hood, and floating shelves that are equal parts functional and gorgeous. Step through to the screened-in lanai and let Florida do its thing. A heated in-ground pool glistens over a paver patio, surrounded by a fully fenced, private backyard complete with a pool shed. A great space for gathering with friend and family, this outdoor space was made for making memories. The primary suite is your personal sanctuary, featuring an en-suite bath and a generous sitting area large enough for a dedicated home office. Both bathrooms have been refreshed with new vanities. The two-car garage offers built-in shelving to keep life organized. And a lawn with a fully automated irrigation system that runs off a private well, without the added water bill. The flexibility here is truly rare. Approved for short-term rentals by the City of Largo, this home works beautifully as a primary residence, a second home escape, or an income-generating investment property. Turnkey setup. Furniture negotiable with a strong offer. All of this, just minutes from the Gulf beaches, top-rated restaurants, shopping, and everything the Coast has to offer. Homes like this don't wait. Neither should you.
Full Property Details
Full Property Details for 1389 Chesterfield Dr
General
- Price: $575,000
- Taxes: $6,700 (2025)
- Status: Pending
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: TB8504519
- Updated: 5/12/2026
- Added to Site: 24 day(s) ago
Rental Information
- Min. Lease: 1-7 Days
Interior
- Number of Rooms: 6
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Thermostat, Window Treatments
- Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer
- Furnishings: Negotiable
- Flooring: Luxury Vinyl, Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Electric Dryer Hookup, In Garage, Washer Hookup
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, Heated, In Ground, Lighting
Exterior
- Exterior Features: Garden, Irrigation System, Private Yard, Rain Gutters
- Deck/Patio: Covered, Enclosed, Front Porch, Patio, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Enclosed, Front Porch, Patio, Rear Porch, Scre
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 33756 - Clearwater/Belleair
- County: Pinellas
- Development Name: 33756 - Clearwater/Belleair
- Subdivision: CHESTERFIELD HEIGHTS
- Driving Directions: Take Bellaeir Rd west to S Evergreen Ave. Left on Ponce de Leon Blvd and right on Chesterfield Dr.
- Direction Faces: West
School Information
- Elementary School: Ponce de Leon Elementary-PN
- Middle School: Largo Middle-PN
- High School: Largo High-PN
Community
- Community Name: 33756 - Clearwater/Belleair
- Pet Restrictions: As per county codes.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric, Heat Pump
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable Connected, Fiber Optics, Public, Sewer Connected, Sprinkler Well, Water Connected
Structural Information
- Architectural Info: Coastal, Ranch
- Architectural Style: Coastal, Ranch
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Windows: Blinds
- Stories/Levels: One
- Square Feet: 1,414
- Sq. Ft. Source: Public Records
- Year Built: 1962
Lot Features
- Property View: City, Pool
- Lot Size (Acres): 0.19
- Lot Size (Sq. Ft.): 8,294
- Lot Size: 8294
- Lot Dimensions: 75 x 110
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Wood
Financial Considerations
- Tax Amount: $6,700
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: CHESTERFIELD HEIGHTS LOT 4
- Flood Zone Info: X
- APN: 272915150840000040
- Property ID: 272915150840000040
Listed by Exp Realty Llc
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Schools
Schools serving 1389 Chesterfield Dr
School District:Pinellas County School District
| Name | Grades | Distance |
|---|---|---|
Ponce De Leon Elementary School, Clearwater, FL 1301 Ponce De Leon Boulevard, Clearwater, FL 33756 | PK-5 | 0.3 mi |
Largo High School 410 Missouri Avenue North, Largo, FL 33770 | 9-12 | 1 mi |
Largo Middle School 155 8th Avenue Southeast, Largo, FL 33771 | 6-8 | 1.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1389 Chesterfield Dr
Date
Details
Price
Change
Source
5/03/2026
Listed
$575,000
25%
MLS
5/05/2023
Sold
$460,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 1389 Chesterfield Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,938
—
$371,540
—
2024
$6,938
585%
$373,351
290%
2023
$1,013
6%
$95,705
6%
2021
$960
-1%
$90,211
-3%
2022
$966
1%
$92,917
4%
2021
$960
4%
$88,965
2%
2019
$919
2%
$86,965
2%
2018
$900
2%
$85,343
2%
2017
$881
4%
$83,588
2%
2016
$850
-2%
$81,869
1%
2015
$864
2%
$81,300
1%
2014
$849
1%
$80,655
2%
2013
$837
—
$79,463
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1389 Chesterfield Dr
1389 Chesterfield Drive, Clearwater, FL 33756 (MLS# TB8504519) is a Single Family property with 3 bedrooms and 2 full bathrooms. 1389 Chesterfield Drive is currently listed for $575,000 and was received on May 03, 2026. Want to learn more about 1389 Chesterfield Drive? Do you have questions about finding other Single Family real estate for sale in Clearwater? You can browse all Clearwater real estate or contact a Coldwell Banker agent to request more information.

